


The Parallels of Pride

by MoonlightIcarus



Series: Bobby Tries New Things [7]
Category: Supernatural
Genre: Anal Plug, Bottom Bobby Singer, Bottom Crowley (Supernatural), Bukkake, Butt Plugs, Butt Slapping, Chaps, Chastity Device, Cock Cages, Crack, Fluff and Crack, Gangbang, Gay Pride, Jock Straps, Leather Kink, Leather Trousers, M/M, Marathon Sex, Military Kink, Orgasm Denial, Orgy, Parallel Universes, Partial Nudity, Pride, Public Display of Affection, Public Nudity, Smut, Sounding, Spanking, Underwear, Underwear Kink, Viagra, hot bear on bear action
Language: English
Status: Completed
Published: 2019-10-09
Updated: 2019-10-13
Packaged: 2020-12-02 01:51:04
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 9,892
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20963318
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: This story tells of two different ways Bobby and Crowley's trip to pride atlanta went.Chapter one is canonical for the series and everything beyond that is just me indulging in as mank kinks as I could think of. It gets out of hand and uncharacteristic for them really fast





	1. Getting ready

**Author's Note:**

> How things really happened

**Summary for the Chapter:**

> They boys need to decide what to wear to pride.

**Notes for the Chapter:**

> This one is canonical as the series moves forward.

"We should go to pride."

"What and why?" Bobby wasn't surprised by Crowley making an objection out of the blue but he was trying to enjoy his lunch. The lunch should have tipped him off because Crowley never made him lunch unless he wanted something out of it. Still he had made good pasta so he could attempt to ignore the demon for at least a little while.

"Pride. It's way everyone who isn't straight goes out and they have fun together. Seeing as I'm a gay demon and you're a bisexual human it's perfect for us". He was sitting across the table using his hands to try and emphasis the importance of it all.

"I know what it its but isn't it in June? You're a little late to be asking about it." He speared more rigatoni on his fork and brought it to his mouth. 

"Usually yes but atlanta has a special pride event this weekend." And there in lies the surprise. It was currently Thursday so that means they could be leaving for it as soon as tomorrow. Emphasis on could because Bobby hadn't agreed to anything yet. 

"Sure." The single syllable was dragged out far longer than was needed and both parties knew he barely agreed to it. "Perfect, tomorrow we can find something to wear and then we can be there on Saturday." "What?" What did he mean something to wear? "Oh would you prefer to go Sunday so you can see the parade?" He knew Robert was referring to an outfit but he wasn't in the mood to show his hand yet. "Why do we need to find something to where? What's wrong with how we normally dress?" This had to be another attempt by the demon to dress him up and force him out in public. He'd done similar things before but those were either at his home or in another country where he wasn't likely to go back to. "Well love, if you dress like you usually do everyone will think you're some backwoods bigot whose there protesting." The hunter sat unconvinced and continued to eat his pasta while eyeing the demon. "Everyone who goes to these things dresses up extravagantly. I'm not saying to change you're entire wardrobe but could you try something other than fifty year old Jean's and flannels?" "I'm only saying maybe for now. When we're actually looking at things tomorrow I'll tell you how I feel about it." Crowley's face regained its usual smirt at the revelation. "But the moment you get too crazy I'm canceling the whole idea." "Alright I'll be more modest with my choices this time around." It wasn't the worst way things could have gone. He still had plenty of options to choose from even eliminating the ones that pushed the boundaries of what was considered descent in public. .... Normally he either woke up alone or with Crowley smothering him. Tobay however he found himself pressed into the demons back with his morning wood pressed right up against that firm ass. He just slightly to flip between those cheeks and started to grind into it. Subtlety was not the intent and even if Crowley were to wake up Bobby doubted he would have any objections to his actions. "Oh, love." The king was awake. "I support your enthusiasm." Bobby moved one arm down from embracing the demon so he could start rubbing into the front of his jockstrap. Once his hand was placed firmly on his bulge Crowley moved his own hand on top of it and started to move them together against himself. In the same lazy fashion he turned his head and abdomen around so he could start kissing his own horny redneck. Bobby continue his slow, simply grinding. Even though he was barely moving it still shifted his prince albert everytime he shifted directions and it made his whole dick light up with the sensations. They continued on like this until they both came in their matching red jockstraps. Crowley didn't even wait for his after glow to end before he was moving out of the bed. As he stood up Bobby was able to see how some of his cum had managed to seep through the fabric or his jockstrap and was sticking in the hair between Crowley's cheeks. When the demon turned his attention was drawn to the large wat spot that had taken over most of Crowley's jockstrap. "Quite staring and get cleaned up. It may very well take us all day to find an outfit for you to wear tomorrow." Even as he said this Crowley was reaching behind himself and when he brought his hand up it was glistening. He gathered the cum up from his ass and was slowly putting each digit into his mouth to be sucked clean. "Ohh!" The filthy display was wrecking Bobby in the wake of his orgasm. "The sooner you get cleaned and dressed the sooner I can cum into that arse of yours and then lick it all back out of you. Or we could do it the other way if you prefer." Even so soon after his last orgasm the promise of sex was a good motivator to get out of bed. He stood and went to the bathroom so he could hurry through his morning routine. Dropping his jockstrap onto the tiled floor he stepped into his shower to quickly rinse off. The only part of he body he really cleaned thoroughly was his dick and inner thighs to make sure there wasn't any residue left from earlier. Everything else was simply run under the shower spray. He turned off the shower and stepped still sopping wet. By the time he started to dry off his face with a towel the adrenaline from earlier had faded and he realised what Crowley's aim was. The demon had fully expected him to rushed out there and agree to some horribly skimpy outfit while he was still thinking about sex. Following his epiphany Bobby went back to his usual pace as he went through the rest of his morning routine. He wrapped the down around his waist and stepped in front of his sink. The hunter pulled out a raise so he could shave the hair that had started to regrow in his pits. The finalxstepxwas to use the beard cream Crowley gave him to get his beard to smooth over and stop frizzing out. He was still running a hand through his facial hair when he stepped into the bedroom to find Crowley in his full black suit. "Alright then let's figure out what your going to wear and what I'll be wearing to compliment it." Bobby wa sput off by the statement, "Wait you're getting dressed up too?" "Why wouldn't I? It wouldn't be fair for you to have all the fun.' He reached into one of his pockets and pulled something out. "Here's the first thing you'll be trying today." He threw it to Bobby and when it was south he saw it was a jockstrap with white straps and a rainbow pouch. They were soon slipped on and adjusted to sit right. "Okay they're on so where's the rest of it?" "There isn't any. That's it." He had all of two seconds before he was receiving a glare. "Alright fine I figured it would be a long shot but I wanted to try it at least." There was a snap and Bobby found a rainbow speedo sitting oh his head. He changed into them and immediately went to test something by setting on the bed. As soon as his ass hit the mattress his suspensions were confirmed about them. Whenever he sat down half his ass would be hanging out of the back

"This ain't happening. Let me rule out a lot of shit at once. If my ass is out I ain't fuckin wearing it." He discarded the speedo and crossed his arms when he sat back down on the bed. "Hie about you give me a short for once you dick." It was fraised as. With a request and a question.

"Alright I'll work on getting something you like but let's put off your upper body until we find something to cover your crotch first. We wont have to spend nearly as much time looking for something that matches if we do it that way."

"Fine." Bobby knew he was in for the long hall so anything so shorten this was appreciated.

And so began their day of trying on clothes. The next thing that tried were trunks but they got the chop when the pair Crowley insisted on kept digging into his skin. This was filled by fitted boxers that seemed good but couldn't work since they were too translucent when they got wet. Even the leather shorts that seemed like a good idea in theory were turned down when Bobby realised he could wear any underwear with them and he didn't like the idea of leather against his dick for several hours. 

Crowley would have liked to follow this with assless chaps but Bobby had already said his peace on baring his ass to the world, so instead he brought up a pair of fitted black jeans. Bobby chose to put on some solid black briefs before he attempted them. He started to get into them when he got stuck at his ass.

"Hey can you help me with these?" The demon wordlessly moved behind him and grabbed the waistband. "Ok now pull." With Bobby getting the front and Crowley handling the back the Jean's came up and were quickly buttoned. 

Crowley quite liked what he saw. They sat low on Bobby's hips but still covered everything well. The material was fitted against his arse but still left space so it wouldn't RIP and let his legs breath. They were straight cut meaning the didn't extend or cull in as they went down those legs so they were showing off a lot but didn't restrict any movement.

"So are do you like then as much as I do?" This had honestly been one of the last things Crowley wanted Robert to wear but seeing it now he would want to see him like this again.

"Let me check." Bobby paced the room, bend over, equated, down and finally set on the bed and they never budged an inch. "Yeah these are goo, so can we move on to something else."

"Yes but just keep sitting there for this next part.

Bobby watched as Crowley got onto his knees at his feet and pulled out a pair of socks. He took one of those feet and slowly worked it on and up his leg, slowly pushing his new jeans up along the way until it sat tightly about three inches below the knee. The process was repeated on his other leg and he like how the expensive material felt compared to the normal kind of socks he bought it twenty packs.

He looked and found Crowley loosening the laces on some combat boots. They clearly weren't made for actual combat because they were the high laced kind that went about halfway up your calf and they had a belt like strap over the ankle and another just below the top, and finally the entire back was covered that were guaranteed to jingle with each step.

By now Crkwley had finally gotten it lose enough to start working it onto Bobby's feet. The hunter was just now realizing the absurdity of ths situation he was in. He had the King of Hell slowly working elaborate combat boots onto his feet so he would have something to wear to a big cat celebration the next day. It was so bizarre he almost wanted to laugh. He didn't when he saw that shoe finally pushed all the way onto his left foot. It had yet to be tied or buckeled and it was already snug on his large feet. There was the possibility of getting a blister but he'd dealt with worse when he had to wear his standard issue military boots so he would cope. The laces were just tightened and Crowley finally went to fasten the buckles of the straps. As he pulled away to start the other boot Bobby took in the feeling of the shoe against the sock and his that felt on his skin. He continued to just lightly shake his foot and get used to the feeling as Crowley worked the other shoe into place on his right foot.

"Alright now stand up."

Bobby did and Crowley straightened out the jeans to lay over the boots. Now that they weren't bunched up only part of the chains along the back could be see and only the buckle around his ankle was visible. Part of the shoes may have been hidden but the effect was still there.

"You should probably walk a little to make sure you won't trip and die tomorrow." He did and had no trouble moving but he would have to adjust to the jiggle that accompanied his everystep.

"Okay I'll be able to wear this now can I have a shirt?" He knew to push the issue or he wouldn't be getting one at all.

"At least humor me before you settle on something." 

"Just show me what you want." He was getting tired of Crowley's incessant tip toeing around saying what he wanted.

"Since you must know it's this." To Crowley hand there was now a gathering of leather straps and metal rings and currently the hunter had not idea when it actually was. "Put at on before you make a decision."

Bobby was going to have to put it on to k kw what it even was.

"Hold your arms out in front of you." As Bobby did he felt the contraption glind along his arms and then felt the demon move is over his head. It was seated on his chest and then Crowley went behind him to start adjust the straps to fit better against his chest. It was nice that the part of the straps against his skin appeared to be made of elastic similar to the waistband of underwear instead of leather.

Once he was finished he created a full length mirror for Bobby to take in his appearance. The chest harness had four straps on it each on about as wide as a belt would be. Two went over his shoulders and the other tow went just below his chest where they all connected to a metal ring resting on his sternum. The straps did t cut into his skin in fact with how they framed him it made his pecs look even bigger than they really were and his nipple piercings were on full display. He went to look at his pants and rheh were hugging his thighs just enough to look good. When he turned to see his ass he was surprised by how shapely it looked in the jeans. Bobby have never been one of those people who found themselves attractive but right now he didn't look like himself and his reflection was hot. However it felt like something was missing.

"Can I get some fingerless leather gloves, a belt, and a leather police hat."

Crowley seemed surprised by the request but soon enough the items appeared on the bed. Bobby started with the belt, even though it was unnecessary it was a nice touch toceveryrhing. Best he went for the leather gloves and secured them to his hands with the small buckles on them. He finished by placing the hat on his head, wrapping his hands around the belt and turning to face Crowley.

Fuck pride he just wanted to ride Robert for the next week with him dressed like that 

"I guess I look as good as I hoped. We can make good on your sex deal in a moment right now I want to see what you'll be wear out there." Crowley now stood in an entirely different out fit and he turned on his feet so Bobby could see every angle. He was wearing skin tight assless chaps with a red striped down the side as well as a leather jockstrap with an accompanying red stripe right down the middle. The chaps were tucked into a matching pair of combat boots. His abdomencwa bear but he had black armbands wrapped around his wrist and biceps and he wore another leather police hat.

"There you've seen now let's get you undressed so we don't ruin your clothes when I ride you until you come in my arse and then sit on your face till I'm satisfied. You better fucking pray nothing catches onto that septum piercing because I'm not fucking stopping.


	2. Getting ready (alternate take)

**Summary for the Chapter:**

> The boys get ready to go out in something a bit more adventurous than last time.

**Notes for the Chapter:**

> This shit ain't cannon so ignore the incsistensies and enjoy the ride.

They had decided to go to pride. They also made a deal that the other one could choose their out fit. But the interesting thing is that they had another bet going.

....  
(Earlier that day)

"I'm sure itll be fun but you probably just want to go so you can sneak off and fuck someone new." Bobby was only joking.

'I'd never do that. No one could ever make me want them like I want you." 

"Then you don't mind putting your money where your dick is." His little joke could have just gotten so much better.

"What is it love? If you've got a wager I'm always ready." He knew any bet between them could benefit him just as much as it could bite him in the ass.

Bobby leaned forward from he is seat at the table as he said, "I say we lock each other in cock cages and sounds the whole time we're there to see which can last longer."

"Sounds surprisingly deviant for you but what does the winner get? There's no point in torturing ourselves if we don't get something in the end."

"If I win I can fuck you while you're still lock up and if you win you can do it to me?" He did his best to sound husky and seductive.

"And what if neither of us gives up during the day?" There was a large flaw in his plan if that wasn't accounted for.

"Well if that does happen then we were both just locked up for a day and we can let each other out to have wild and crazy sex." 

No matter what he would get sex and even on the extremely unlikely chance he gave in he could always take it out on Robert's arse next time. "Deal we can lock each other up when we get ready tomorrow."

....  
(Getting ready)

Bobby was the first to get locked up. He was sitting naked on the toilet seat while his demon was on his knees between his legs. Crowley had made a custom cage to account for his prince Albert. The cage was made of two separate parts that came together at the bottom and could be screwed shut and then locked. It had a special hinge that allowed it to close in a way that wouldn't pull on any hairs and wouldn't poke out in any way. There was also a band (this was made of silicone not metal) that wrapped around the base of his cock and went behind his balls to push them forward, away from his body. "Uhh that's weird." There were now a series or rings wrapped around his cock that kept it bent at an angle and prevented him from getting hard. The head was nestled in a sort of dome shape with a hole at the end for his slip and a special opening at the bottom for his prince Albert. "God, it's just loose enough to not cut into me. You think you might have been cutting it a little close?" "Not at all love. You may want to grip my shoulders for the next bit." Bobby fully believed the warning and moved his hands to grip at the shoulders in front of him. Crowley brought the lubed sound up to the opening at the tip. The sound was extra long and covered in bumps. Both the bumps and the sound itself were large towards the end and be slowly started moving it in. "Oh God, this shit ain't right." Even as he protested Crowley continued to slide it into his dick. "Stop winning. This was your idea and besides you always have the option of giving in so I can fuck you once I put it in." The seasoned hunter was already this loud and needy and they'd only just gotten started. He was about halfway in and the bumps kept growing in size. "Fuck. Fuck. FUCK!" "Just a bit more and...done. Now to keep it in place." There was a small bar at the end of the sound and one on either side or the cage surrounding it so a lock could be thread through to keep it in place for as long as it needed to be. Crowley moved the key to the cage and the key to the sound away into hell where they'd be safe and sound (he would never say such a horrid pun out loud but he was still proud of it) "Now as soon as you feel up to it you can do me and we can get dressed." He was enjoying the way that hefty cock still looked big and well developed even when locked up tight. Bobby was still grasping those shoulders even as he moved to stand up. "Sit down. I'm not going to suffer like this and let you off easy." "Right away love." Crowley moved to sit on the toilet while Bobby took his place on the floor. The hunter picked up the larger cage from the ground so he could get started kn evening the playing field. Each set of cage and sound was proportional to the other. Crowley was a demon but all was fair in sex and war. This meant that not only was the cage longer and wider to accommodate he large size but the sound was also stretched making each bump longer than it was on the sound nestled into Robert's shaft. The whole process was very similar to the one earlier with the cage being locked around his soft (but still massive) cock while allowing his prince albert to hang through the end and the sound being put in at an agonizingly slow pace that was only made worse by how Robert's hands were slightly shaking. As the end of the sound aligned with the cage he could feel the tip of it pressing in past the base of his cock and he understood why Robert chose to chant fuck earlier. Soon his was also locked into place and hs helped the hunter get up off the floor. They held onto each other as they panted and stared down at the cages. Both of them were locked up and encased in metal while their balls were being shoved forward. "So were stuck like this for the long haul then." He chuckled at the end to try and distract himself from the foreign sensation of something being shoved into his dick. "Fraid so. Now we need to get dressed so we can head out and enjoy our fun." They moved together to exit the bathroom and as they did Bobby felt a hand push him to sit on the bed as Clowley walked into the center of their bedroom. "Since you went first last time I'll go first now. So what did you decide I should wear today." Rather than wasting money on clothes they decided to just have Crowley create what they would need and wait to tell the other their plan was when they got dressed. "A red speedo like you wore in Scotland. The kind that pushed you dick forward in a pouch and was so low in the front that part of your bush is still sticking out. The back needs to stick to your ass without sliding into your crack. I want you to wear a matching red butt plug thats seven inches long like my cock with a foot long tail sticking out if the back that curves onto the small of your back." He decided to end his demands for now and just let Crowley do the first part of his list of requests. Crowley did just as desired and was now wearing the described items. "Come over here so I know they fit right." "You're always so needy." He moved over and let Bobby check that they fit biw he wanted them to. Fingers were stuck in each opening to make sure the speedo was tight enough and he tugged on the tail to make sure it was lodged firmly in that ass. Satisfied he gestured for Crowley to resume is place at the center of the room. "Now put on a red leather chest harness that only covers the top of your chest with some red wings right onto your shoulder blades. I want them to stick out an inch past your arms when they rest by your side. Also put some horns on your head. Little red ones that are about three inches big and curve inward." The requested harness appendages appeared like he asked. The little red bat wings sat there just as adorable as he imagined and the little devil horns on the top of that head got surrounded by that messy hair where they connected to his skull. "This will do nicely but make sure it stays tight and the wings stay up right." "I figured as much. I'm not daft." He was already growing annoyed with this blasphemous clown suit. "And to finish put on some red ankle socks and red high top converse." While he could have gone with goat hooves or something to better match the rest of the look, the entire purpose of these was to piss Crowley off. The posh King would be seething by the end of the day if he was forced to wear such cheap things. "There's everything I had planned now enjoy your turn." Crowley already hated the shoes and socks just from the short walk to switch places with Robert. He was a king not some oaf who wore shitty mass produced sock from a bargain bin. Getting Robert dressed was sure to be therapeutic for him. "Here's the first item." Bobby looked and saw a white jockstrap by his feet, and when he picked it up he noticed that it was the oldschool kind that had the sort of wavy fabric that was made to stretch farther to accommodate bigger dicks. Looking even closer he realized it was worn, faded, and starting to fray at the sides, it was by no means dirty but certainly had been unused thoroughly before. He tried to avoid the thought of putting on someone else's old used jockstrap and became slightly thankful the cage at least blocked some of his skin from direct contact. Once he pulled it onto his hips he realized it was a size too small. The straps and waistband were digging into him and the pouch had stretched a fair bit with his his package was being emphasized to where the outline his dick and balls were clearly visible but you couldn't tell he was wearing a cage. "Isn't it just amazing what some people will donate to the Salvation Army. Next up put this on." There next to him was a pair of what he recognized to be standard issue military socks. Just like with the jockstrap he noticed how they were faded and had patches where the material was noticeably thinner than others. He moved to sit on the ground and momentary regretted it when he jostled his cage but he did his best to ignore it and get the socks onto his feet. They seemed to be half a size too small but thankfully had enough stretch to cover everything from his toes to the area above his ankle. "Dont bother getting up just yet you still have to put on your shoes." The shoes were like the socks the standard issue military shoes you wore in training, battle, or speaking at an informal public event. He preemptively check to make sure they were the right size for his feet. While enlitsted he learned that most of the shoes that were issued ran small and had little to no room inside of them. Thankfully the shoes were indeed the correct size, so while it would still be a tight fit he would be able to fit his foot inside without completely crushing his toes. Even still they took a bit of effort to get on and even longer to get correctly laced up in the proper military style. "Okay you're good to stand up now." As he was getting up Crowley also came to stand near him. He stretched out his hand and gave Bobby a military issued camo hat. Unlike the other things it appeared to be brand new and never worn before. The hat was bigger than necessary so instead of being able to wear it correctly with it tightly against his skull so he just put it on like he would one of his trucker caps. "Is that all you've got?" All Crowley could think of was a sexy soldier, he knew his idea of making the King of Hell dress like the devil wasn't clever but it at least had more parts than this. The only reall challenge was that he couldn't bend over without flashing someone with his asshole. "No love. You've still got a bit more." Snap "Ohh," he moaned at the feeling of a large plug suddenly inside of him. If he had to guess it was probably seven inches long just like the one Crowley had in him. He knew he wasn't torn but it was still something he had to adjust to. There was certainly no way be could sit down now, between having a plug in and having his ass bared for the whole world too see he would be stand up the entire time. Crowley moved to stroke over his back in a soothing manner. "Dont worry it's almost over now." He continued the soft movements until he suddenly stopped and smacked Bobby's ass hard. Then he heard the familiar sound of Crowley's phone taking a picture and he turned around to see what the demon was up to. He was rubbing over the spot that had just been struck when he saw the image on that phone. Taking up his entire back was the phrase "SMACK MY ASS FOR THE TROOPS" It was done in the same font as the old "I want you" adds that they put on posters. It was perfectly clear and looked like a tattoo. He could also see where there was a red handprint on his ass from Crowley's smack. "Don't you just love how now you will know exactly who supports out troops out there today. And you'll be extra glad to know I got your jockstrap, socks, and boots from the Salvation Army store in town and your hat from the army surplus store. This is much less wasteful." Bobby wanted to make a retort but he was interrupted by the demon. "Come on let's go so we can enjoy the festivities and find out who supports those who protect and all that jazz." Next thing he knew Crowley had a hand on his shoulder and was moving them to Pride.


	3. I'm turning red

**Summary for the Chapter:**

> The people at pride either love the troops or will take any opportunity so feel a good ass

When they arrived they were standing outside a large metal gate with the words "Piedmont Park" written across the top of two smaller gates that were on the sides of it. Bobby could feel the breeze on his ass and saw several tents and people inside the fenced in park. He was getting aroused at how indecently he was dressed but it didn't last long with the cage in the way. Turning he could see Crowley sporting a devious expression and he only spent a moment regretting his decisions before he remembered what was on the line. "So it's just in this one park. I expected more." At least if it was a small even there wouldn't be a lot of people who saw him like this

"Actually love this is a rather big park and I aim to see as much of it as we can." He began to walk ahead through the metal gates while Bobby quickly moved to walk alongside him. As they came in the were greated by a young man and a police officer stationed by the entrance.

Past the gate they could see a few shaded booths and could already feel the drum of the loud blasting music. They went past the first aid tent and the car sponsors positioned at the front and went towards the actual festivities.

When they came to a fork in the paved path Crowley spoke up. "Come on let's go to the left. We'll loop back around and see the rest later." He again moved on ahead before Bobby had a chance to react.

He led them up a small hill (it was so small Bobby wasn't even sure if it qualified as a hill) that had been flattened off and had several flags resting on the ground that could be walked between. There was the standard rainbow flag but beyond that each one was a quilt stiled one mean to honor a specific person. They had names, dates, and imagery to represent each person, one even had the dragon that appeared on the Welsh flag.

"So it's a memorial to people who made a difference?"

"Yes each person here worked to make progress in gay rights." Even as Crowley finished they both went to examine the different flags. They had looked at each one before returning to follow the path again.

The path had a lake to one side and a large grassy field with a stage and tents selling alcohol to the other. From what Bobby heard of the comedian currently performing they were failing miserably. Even if the jokes were funny then just couldn't get a reaction out of the crowd. Bobby sped up a little to avoid the trainwreck of a performance. Next they came upon another fork in the road with the side to the right advertising food and the left having stalls and sponsors. The hunter didn't even wait for Crowley before he moves to the side away from the food. He didn't like the idea of eating shirtless and getting grease and condiments on himself.

Walking ahead Bobby felt the first strike against his ass. After he recovered from the shock he turned to see the perpetrator and saw it to be a man that was also shirtless. He was only wearing cargo shirts and sandals which showed off his hairy muscular torso. His hair was close cropped onto one side and folded over onto the other. He was sorting a grin so cheeky it could have rivaled Crowley.

"Sorry, hun, I was just doing what the sign said."

"Well that's why it's there, ain't it." He wasn't going to let it get to him and was relieved when the man chuckled and walked away.

"Well I see you made a friend." Crowley had just come up next to him and handed him a large lemonade. "They make it with a special vodka that sponsors the event." Bobby took a sip and noticed it was definitely meant to be had more for the vodka than the lemonade. Only now did he register that Crowley was sipping on his own lemonade.

"I'm surprised you're even drinking this junk given how you usually hate anything not topshelf." They both took sporadic sips as they continued down the path.

"Well it's not a proper American celebration if you don't waste money on twelve dollar lemonade."

They moved past the banks and credit unions that were giving away pride flags with their logos on them. They only glanced at the three booths that seemed be to sell only fans. At one point Bobby went to look at a stall selling metal necklaces on leather cords. They looked nice but when the heavily muscled shopkeeper told him everything had a base price of $120 he decided against it. As he turned around he felt the man reach over the table to land a hard smack on his ass that echoed around him. He chose to move through the pain and walk away without acknowledging it.

As they walked by what Bobby knew were classified as bears (after all he was one) with their hairy chests, thick beards, and heavy muscles he felt all seven of them land an open palm slap against his ass. Two of them even lingered and squeezed after making contact. It took too much effort to avoid reacting so he let out a few quiet moans toward the end and was eternally grateful no one mentioned it even though he knew they must have heard it.

Crowley pulled him aside to a stall that was selling baseball caps and buttons. While the demon found an item and went to go purchase it Bobby leaned forward to get a better look at a hat when he felt a strong hand land right between his asscheeks and hit the plug there.

"Uuh." This was not a sound he wanted to make in public but the plug had agitates his prostate when it was hit. He realized when he bent over that the plug must have been showing so someone decided to seize the chance.

"Here you are love." Crowley had apparently paid during his encounter and he was currently holding up an enamel pin with a bear paw on top of several brown lines in different shades. When Bobby tried to take it he pulled it back.

"What is it exactly?" He also wanted to know why Crowley wouldn't let him have it but one question at a time.

"It's the bear pride flag with a bear paw on the front for emphasis." The demon took Bobby's military hat and began to place the pin just to the left of where the brim ended. From there it would be visible from both his front and left side. "It only seems right to have something representing what you stand for." He put the hat back on Bobby's head in a way that the slightest breeze would blow it away.

Bobby went to fix the hat and said, "If you think so then why don't you have one?" He finally got it put on right and was glad when the pin didn't dig into his skull.

"But I am love." He pointed to a matching pin that sat on the strap of the harness that went over his left shoulder.

"Ugh, fine. Come on there's more to do now that you've bought your pins." He grabbed the demon's hand and went across the short bridge that went over a narrow portion of the lake.

Walking across they saw a playground that was surprisingly bustling with children. Bobby figured it was the kids of some adults who came to pride or at least came to show their support. They passed some restrooms and found another large group of stalls. One in particular was selling kilts and Crowley got one that was black on the outside but between the flaps there were streaks of color that formed a rainbow. He paid and then as subtly as he could sent it away so he didn't have to carry it around with them. When they went by a vacation lottery Bobby felt another hit against him. 

"Are you really starting to feel it love." Crowley really was the devil for coming up with this horribly efficient plan.

"Yes, it feels nice to get attention from someone other than you." Never challenge Bobby Singer because the bastard will always go down swinging.

The kept going until Bobby saw a shop he wanted to stop at. It was just a tee shirt shop but everything was simple and easy on the eyes. He knew why the rainbow flag was the gay symbol but the constant neon wasn't helping his vision. 

"Do you have this one in an extra large." He gestured to a simple shirt that was a dark grey blue with the silhouette of a bear (the animal) and it was filled in with a red flannel pattern.

"We may. Did you want the tank top, tee shirt, or long sleeved one." The man behind the counter was another well built man but this time he did have a shirt on.

"Tee shirt."

"We do. It'll be forty five dollars."

Bobby knew he didn't have cash but he did have a demon with a seemingly endless supply to blow through. "Hey Crowley can you lend me some cash."

The demon stopped where he was looking at a harness shop and came over to him. "Of course love. How much is it?"

"Forty five dollars."

Crowley pulled out his wallet (the poor cashier probably thought he had literally pulled it out of his ass since he had nowhere to store it) and handed the man a fifty dollar bill. "Keep the change and happy pride."

He responded, "Happy pride." And handed Bobby the shirt before it was passed to Crowley to get sent back to the house.

They came to a dead end and turned around to head down a different path. This one was full of more shops and more food carts that seemed to only sell mixed drinks. Along the way they saw a group of protestors. At first they didn't even know they were protestors because they were completely surrounded by a group of counter protestors who were blocking all their signs with their own signs. Then one of them walked off to the side and started to tell everyone he passed that they were going to hell. He even came up to Bobby and Crowley.

"Don't you realize that you're getting in bed with the devil." The protestor was trying to make them feel guilty but he didn't know the irony of his statement.

Bobby wasn't going to let the bastard win so he pulled Crowley into a kiss and started to grind into him for dramatic effect. He really laid it on thick and even moaned into Crowley's mouth. Before pulling back to say, "I know that and the devil happens to be excellent in the sheets." Crowley put a cherry on top by flashing his eyes red at the man before he ran away back to the crowd of protestors.

"Well that certainly left an impression." Bobby was still pressed against him when he felt another slap to his skin.

"How's that rump doing love? I'd love to fuck you when it's nice and cherry red." He whispered the second half incase any children were nearby. 

"I could keep this up all day. I've lost bets to you before but I'm not losing this one."

"I'm glad you feel so confident today. Now how about we go where the real fun is."

Crowley was moving farther down towards a small gate with a body guard standing in front of it.

"No admittance without ID's." The guard looked like he had to deal with a number of people who didn't want to cooperate that day.

"Of course here you are." Crowley handed him an ID for both himself and Bobby before the guard stepped aside and let them through.

"Crowley what is this?" He had only just walked through when he asked.

"Its a 21 and over area."

The area was a large brick and stone plaza area that partially hung over the lake. There was a DJ blasting music with a strong bumping beat and next to him was a black tent that said bar on top of it. But what was the most important thing were the people down there. It was entirely bears. Everyone was heavily muscled and shirtless to show off their chest hair. Nearly all of them had big thick beards or at the very least a good mustache, and they were wearing everything from tight cargo shorts to trunks and briefs that acted like a second skin all the way to a few who were also in jockstraps like Bobby.

"Did you want a drink?" 

"The strongest thing they have."

Crowley nodded and went over to the line for drinks while Bobby started to think about revenge. His ass was going to be sore no matter what so it was time for overkill and time to make the demon jealous. Bobby move over to a thick ground of people when he pulled one against him and they started to rub against each other to the beat. He didn't know how to dance but he knew how to sell being horny and desperate. He kept going and then he moved to someone else to continue the process.

Suddenly his butt was hit with one of the hardest slaps yet. "Is this ass free?"

Bobby continued to grind against the man in front of him and only turned his head to look at the wall of muscles and tattoos when he responded, "No but you can always try and get some without being indecent." He went so far as to shake his ass.

The man molded himself to Bobby's back and began rutting against his ass and rubbing all along his back. This pushed the hunter over further into the guy in front of him and it was setting his nipples on fire. He kept up the dancing and partner changing when one guy went to grope at his dick through his jockstrap and was surprised when be felt metal there.

"Surprise." 

"I see you've been enjoying yourself." Crowley now stood about two feet do Bobby's left and in each hand was a red solo cup.

"Yes I am." He took one of the cups from Crowley and chugged it. It seemed to just be vodka with a splash of grenadine but he didn't really care about the flavor. Then he turned to the current guy gring into his ass. "What's your name?"

"Clement." The answer was a rough grunt.

Bobby then pulled away and place himself beside Crowley when he looked behind him. "What's redder my ass or his speedo."

"I'm gunna have to say his speedo." Clement seemed a bit confused by the question.

"Well could you guys help get both these asses that red."

"Fuck yes. I'll go get everyone on board." Clement and the one Bobby was grinding into moved out to spread the word.

'Robert Singer you fucking heffer. I love you when you want to get even." He pulled him into a short chaste kiss.

Soon Clement was back and instructing them, "Hey come on over this way." They followed him over to a raised ledge where they could lean over and stick their asses out, and they did just that.

"Remember guys we need it as red as my speedo so don't even try to hold back." Robert may have organized this but he was going to make it even worse.

And so began the long process or everyone spanking their asses to get them fire engine red. Each guy would come over and hit them as good as he could. Usually they were met with groans but occasionally Crowley or Bobby would give a response like "that the best you got", "put your back into it", "I need it to be red", or "harder". Each one was met with the offended party going at it with more gusto and power behind their swing than before. Sometimes after they made contact the guys would rub over their asses or grope and squeeze them before going in for a follow up smack. 

Even though Crowley was wearing a speedo you could still see half his ass so they were able to tell how red it was in comparison to Bobby's. After what they assumed was everyone someone took a picture and showed it to them.

"I was expecting it to look better." Bobby was disappointed it was only a dark pink and not the red he wanted.

"Are we sure we got everyone?" Crowley looked around and saw a few people he knew weren't there earlier. "I think we missed a few and since I'm not sure who was left out everyone will just have to do it again." He was sure to be extra loud when he said it. The proclamation was met with devilish grins and a few cheers from all the people around them.

They resumed their positions and the bears behind them resumed their assault on their asses. This time most of the guys would partner up for it. Two guys would be on each one of them and everyone had hit them at least two or three times each. When they were shown the new picture of their asses they were much happier with the color. Then Clement came up to them followed by the wall of muscle and a few other guys.

"So you guys seem to be enjoying yourselves, do you want to come back to our place and really get things going?"

"Should we love? We've still got a bet going."

"Crowley I'm ready to take on anything right now." The vodka and the musk was really starting to get to him but not enough to impair his judgement just remove his inhibition.

"You've got a bet going?"

"Yeah we're both sporting cockcages and sounds and whoever asks to be released first gets fucked by the other while they're still locked up." Bobby had lost all care in the world. He was never going to see these people again.

"But feel free to shag us while we're still like this. It'll make everything more interesting."

"Fucking kinky bastards. Let's hurry back before we fuck ya right here.

**Notes for the Chapter:**

> Next chapter is an orgy where neither one wants to give in.


	4. It keeps going

**Summary for the Chapter:**

> They make it back to Clement's apartment and enjoy several hours of hardcore fucking.

It was only a few blocks before they made it to the apartment building Clement was staying in. They went in past the lobby and the woman behind the front desk didn't seem to even register that they had come in. They all pilled into one elevator. It was by no means small but it could comfortable fit about ten regular sized people not the eight large men currently cramped together inside of it. The small space did however give them the opportunity to start groping and rubbing against one another. The doors eventually opened and they exited it still clumped together in the aroused huddle. They enentaully came to a door which was swiftly opened by Clement.

The room on the other side was a very modern room. It was all vinyl couches and sleek plastic tables and lamps with a TV mounted on the wall and a large glass window encompassing one whole wall.

"You ever had a good view of the Atlanta skyline?" They just shook their heads at the question. "DO you want to get a nice long look while we fuck you?" Clement continued.

"Hell yes." bobby then moved over to the large glass wall and rested his hands against the glass while arching his back to present his ass. Crowley follow and did the same about a foot to his left.

"You boys don't even need to prep us we've both been plugged up all day so just pull them out and start having some fun. oh and Just twist the tail clockwise to get it to pop out." Crowley was more than ready to watch Robert slowly be fucked into a hazy stupor before he finally begged to be released from his cage. This entire day was worth it just for the visual of Robert ruined from hours of teasing without an orgasm.

"Didn't you guys say you were having a bet to see who could last longer in a cage." This time it was just one of the other guys who asked the question.

"Yeah I thought we were pretty clear on that>" Bobby figured if they wee going to fuck him the least they could do is get on with it.

"Well what if you took some viagra to see who really has the better stamina?"

Bobby and Crowley looked to each other as if they were having a silent conversation before Crowley answered, 'Yes but make sure we get to each. Wouldn't want to spoil the fun with too low a dose."

Soon they each had tow little blue pills in their hands and dry mouthed them without even standing back up. Then the guys behind them moved to pull out their plugs. Bobby's was easy enough with nothing in the way, but Crowley's had some issues. While the tail came off easily enough the guy was having a tough time trying to remove the snug speedo so he could reach the plug.

"Just fucking cut the speedo and I'll deal with it tomorrow." The request was carried out by a packaging nice that was carefully, and quickly slicing it to pieces. When it all fell away the cage encompassing his cock was finally exposed.

'Shit, the brit's hung like a horse."

"Well since I cant currently use it would you please get on with it and fuck me in the ass sometime today."

Clement then came up behind Bobby and the largest man came up behind Crowley. Crowley felt the plug being removed swiftly and then felt how he was being speared open by what had to be at least an eight inch cock.

"Fuck." Clearly Clement was similarly well endowed if that was Robert's reaction.

Then they could both fully feel the effects of the viagra as they were heating up and kept trying to get hard even through the cages. The men the moved inside of them. Neither one held a steady pace, seeming to focus only on their pleasure and not the men who they were fucking. and to be fair they knew why since the demon and the hunter where unable to truly enjoy it. 

Eventually the men came inside of them and were replaced by two other men. When the next guy pushed into Bobby he could feel the prince albert rub against his insides and graze his prostate on each pass by it. The man had mounded himself to Bobby's back and placed his hands on top of the hunters as he took short shallow thrusts. The one currently fucking Crowley instead chose to use slow, long thrusts. Each time he pulled out he also pulled down on Crowley's nipple rings to make sure he was feeling it all over.

This came to an end too soon as well and by the time the third round of people entered them they were too blissed out and frustrated to care. When they had finished the pair assumed the fun was over until someone patted on their sore asses.

"Come on let's head on over to the bedroom. We all took some viagra and we're ready to go for another round.'

They let themselves be led onto the bed where they laid down on their backs with their legs bent at the ankle. Bobby wasn't took exposed since they never took off his jockstrap but Crowley was completely out for the world to see. This time Clement went for Crowley and the massive wall of muscle there Bobby's legs over his shoulders. The large man certainly had the thicker cock but Clement seemed to have a better idea of how to use it. The squelching sounds they now produced from all the cum left inside them only turned everyone on more.

For the next round Crowley had to furn over onto all fours while Bobby was taken in the missionary position. All the cum they were stuffed with was causing their stomachs to protrude slightly, but you could hardly tell because of how big they were to begin with. The found after that Bobby was doing it doggy stile and Crowley was in missionary, and just like before these men were incredibly unremarkable.

They then got arranged to have their bodies pressed against each other for one final round. Clement again took Bobby's ass and the large man Crowley's. But this time the other for men were kneeling on the bed and stroking themselves to the sound of the two men being fucked. Bobby and Crowley wrapped their arms around the other and began to sloppily kiss and rub against them in a way that agitated all of their piercings. Every so often the thrusts would line up and they would be shoved closer together which resulted in a metal clink from the cages coming together. The men who were stroking themselves moaned at the sound.

One by one each of the mean surrounding them came on their sides and started to rub their semen into their skin to mix with the sweat. It all culminated in the final two orgasms that released inside of them. When they were pulled out of this time the plugs from earlier were pushed into place to keep all the loads of cum inside.

'Hey do you guys want to stick around and stay here for the night." The questioned was asked honestly and not as a way to get more sex.

Crowley didn't feel like moving but he wanted the cages off so he could finally achieve release. "Thanks for the offer but I think it'd be best if we got back to our room and unlocked ourselves. but would you be able to give me something to wear outside?"

"Sure thing." Clement went over to a dresser and pulled out a black jockstrap. Crowley knew it would be a tight fit that would still leave part of him exposed but it didn't matter since the moment the apartment door closed behind then he was going to transport Robert ad himself back to the house.

Once Crowley had put on the jockstrap that was as bad as he predicted he went to wake Bobby. "Come along love. We've got to get back now."

"Uh." Bobby could feel all the cum moving around inside of him. He wanted nothing more than to have Crowley yank the plug out and remove the cage so they could fuck until the passed out. He followed Crowley out the door without saying goodbye and was relieved when they were immediately taken home.

Once they were at the house Bobby was surprised that Crowley didn't tackle him to the ground, no instead they simply leaned heavily onto one another.

"Listen love. How about we unlock each other and then take turns fucking again and again until were both sated? And while one of us tops they will have their plug removed so they can feel all the semen currently inside of them slowly drip out and make a mess of their arse and bollocks."

"Get your fucking keys."

It was a very long night.

**Notes for the Chapter:**

> and so another work comes to an end.


End file.
